Foot in the Door Questions

These questions consist of icebreakers which you can throw in when you initially meet.

They’re nothing deep nor invasive, but just have the right amount of curiosity and fun.

Keep it friendly and clean for the first meetings just to make sure that you both don’t get overwhelmed nor uncomfortable.

Which college did you attend?

Do you like traveling?

What was your favorite class back in school?

…And your least favorite subject?

Do you play any instruments?

Which movie genre are you into?

Are you a fan of sweets?

Are you a gym rat?

What was the first thing you purchased from your first paycheck?

Are you an adrenaline junkie?

Which season do you like best?

What was the craziest thing that you did while drunk?

What’s your favorite foreign country?

Do you enjoy your job?

Have you ever had a really bad workmate/boss?

Do you like watching horror films?

Do you know any foreign languages?

What’s your family like?

Which do you prefer: downtown or city?

Have you ever considered moving to a different state/country?

What was your major in college?

When was your favorite vacation?

Can you tell me about the worst professor you ever had?

When was your first kiss?

What’s your favorite cuisine?

Lifestyle Questions

Now that you’ve gotten past the awkwardness of the first meeting, you can already try asking them a little bit more about their lifestyle.

You can start with their hobbies and interests, moving on to more serious questions like stress management and even finance.

How often do you exercise?

Do you smoke?

Do you know how to cook?

Are you the type to buy his own house or rent an apartment in the city?

What do you usually eat for breakfast?

At what age did you buy your first car?

Are you the type to often join lotteries/raffles?

Have you ever considered building your own business?

…What type of business do you have in mind?

Do you like staying in or going out?

Chinese takeout or pizza?

Dogs or cats?

Do you have a pet at home?

Do you like going on a nature trip?

Can you hold your alcohol?

Are you the type to risk investing in stocks or just secure your savings in the bank?

What was the most expensive purchase you made for yourself?

Do you like shopping online?

When was the last time you’ve been admitted to a hospital?

Are you a morning person or a night owl?

Do you like buying branded things?

Are you the type to always watch his diet?

Do you like going tnightclubs/bars?

Do you like swimming/going to the beach?

Do you have any sport?

Provocative Questions

As you get to know each other, it’s inevitable that your conversation leads to some steamy questions.

While it’s expected that you give witty and playful answers, you have to make sure that you’re also prepared to ask equally naughty questions!

Remember, two can play at this game!

What’s your biggest turn on?

Do you like sub women?

How much of a dom are you?

Do you like angry sex?

At what age did you lose your virginity?

What’s your favorite position?

Lights on or off?

Where’s the craziest place you ever had sex?

Have you ever made out with a friend before?

What’s your favorite porn category?

Are you a butt or boob person?

Worst one night stand experience?

Have you ever experienced someone walking in on you and your partner?

When do you consider a girl hot?

What’s your biggest sexual frustration?

Do you like going down on women?

Do you have any sexual fantasies with someone you know you’ll never have?

Are you into younger or older women?

Do you like seeing your girl in lingerie?

When’s the best time for sex?

Do you find car sex hot?

What’s the dirtiest thing you did in public?

What’s your biggest kink?

Have you ever been intimate with a person from a different race?

What’s your most awkward sexual experience?

Personal Questions

It can be quite tricky when you get down to this part: personal life. These can be about childhood memories, fears and dreams.

As this can show vulnerability, your manner of asking will surely determine how someone will open up to you. Make sure you sound sincere and you don’t look intimidating.

What’s your greatest fear?

How was your childhood like?

Do you have any traumatic experiences?

What do you think of depression and other mental health issues?

How do you deal with heartbreak?

What was the worst pain you ever experienced?

Have you ever been with someone who is too manipulative/controlling?

Do you get jealous easily?

What was the craziest thing you did for love?

What age do you plan on settling down?

How many kids do you see yourself having?

Do you get along well with your family?

What is your biggest pet peeve?

What do you like most in a person?

Do you like strong personality or timid ones?

Who is the person who has the biggest influence on you?

Have you ever cheated on someone?

What’s the worst thing someone ever did to you?

What’s the worst thing you ever did to someone?

Do you find it hard to say sorry?

How do you handle arguments?

How do you balance your personal life and career?

How do you confront a person?

What’s the worst lie you ever told your partner?

What’s the cheesiest thing that you did for someone?

With these questions, you can easily ease in to a much more comfortable and closer relationship with that person you’re eyeing.

The most important thing to remember is to show genuine interest whenever you get to talk. You also need to be observant with how he reacts, taking note if he is into the conversation as much as you are.

Lastly, timing is always everything. Know when to ask which type of questions! You need to always feel the vibe before throwing in your questions and comments. Good luck!

For more mindful and practical self-improvement advice on your Facebook newsfeed, like Hack Spirit on Facebook:

A quick message from Lachlan Brown, the founder of Hack Spirit

In 2018, the third year of Hack Spirit, I poured thousands of hours and considerable resources into creating these articles. It's a labor of love and remains free thanks to your patronage. If you found any value in these articles, please consider supporting what I do with a donation. Your support is what helps me to continue creating more Hack Spirit articles. To make a donation, select the amount and click the "donate" button below.